Earn point on your loyalty program!arrow arc left

Cheap flights from Boston (BOS) to Chicago (CHI)

Know your dates, get live prices in seconds
airplane logo

pin logo

calendar
Departure
calendar backward
Return
airplane logo
1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
Book Flight + Hotel at the same time

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.

Cheap flights from Boston to Chicago in November , December 2026

18 Nov - 10 Dec $ 256.00
BOS
Boston
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
BOS
Boston
Pick dates
23 Nov - 24 Dec $ 289.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
Pick dates
19 Nov - 08 Dec $ 315.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
Pick dates

Last minute flights from Boston to Chicago

18 Nov - 30 Nov $ 393.00
BOS
Boston
JetBlue Airways
1 STOPS
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
Pick dates
23 Nov - 30 Nov $ 398.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
Pick dates
19 Nov - 30 Nov $ 426.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
Pick dates

One-way flights to Chicago from Boston

12:39 PM - 5:00 PM
Frontier Airlines
1 Stops
6h 51m
BOS - CHI
$ 146
Kiwi
Pick dates
2:40 PM - 2:40 PM
JetBlue Airways
0 Stops
3h
BOS - CHI
$ 163
Kiwi
Pick dates
2:40 PM - 2:40 PM
JetBlue Airways
0 Stops
3h
BOS - CHI
$ 165
Kiwi
Pick dates

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

Related info for your journey
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.